Sumitomo Chemical Company, Limited

Eiichi Murayama

Masayoshi Minai

Shunji Aono

Yoshio Suzuki

Noritaka Hamma

Takenari Nakagome

Toshiaki Komatsu

Yasuko Eda

Akio Izawa

Hideo Agui

Mitsuo Nakashita

Toru Mitani

Kousaku Okamura

Toshihiko Hibino

5-Carboxy-2-acetylthiophene, which is useful as an intermediate for the production of a therapeutic agent, can be prepared in a high yield by the selective oxidation of 5-acetyl-2-thienylacetic acid or its derivative with a particularly selected oxidizing agent, i.e. permanganate.

Process for producing 5-carboxy-2-acetylthiophene

Bisphenoxy carboxylic acid derivatives useful as an antiarteriosclerosis agent with good absorbability and low toxicity, which are novel compounds represented by the general formula, ##STR1## wherein R.sub.1 and R.sub.2 represent hydrogen atoms or lower alkyl groups and A preresents ##STR2## (wherein in case R.sub.3 is a hydrogen atom, R.sub.4 represents an amino-lower-alkyl group, an N-lower-alkylaminoalkyl group, a heterocyclic group, or a heterocyclic group-substituted alkyl group; or R.sub.3 and R.sub.4 may join through an intermediary hetero atom to form a heterocyclic group and if said hetero atom is a nitrogen atom, this nitrogen atom can bear a lower alkyl group as a substituent) or ##STR3## (wherein R.sub.5 represents a hydrogen atom, a hydroxyalkyl group or a derivative thereof, and R.sub.6 represents a hydroxyalkyl group or a heterocyclic group; or R.sub.5 and R.sub.6 may join to form a cyclic group, or may join through another intermediary hetero atom to form a heterocyclic group and if said hetero atom is a nitrogen atom, this nitrogen atom can bear a lower alkyl group as a substituent).

Diheterocyclic esters of 4-(1,1-bis-(phenoxy-propionic or -butoyric

Novel anti-atherosclerosis agents having the formula, ##STR1## wherein R is hydrogen or lower alkyl, n and m each signify an integer of 4 - 6, and A is hydrogen or a group of the formula, ##STR2## WHEREIN R and m have the same meanings as defined above. These compounds are produced, for example, by reacting a bisphenolic compound of the formula, ##STR3## with chloroform and a ketone compound of the formula, ##STR4## in the presence of an alkali. Alternatively, they are produced by reacting the bisphenolic compound with .alpha.-halogeno- or .alpha.-hydroxycarboxylic acid derivative of the formula, ##STR5## wherein R and m have the same meanings as defined above, and X is halogen or hydroxyl.

Phenoxyalicyclic carboxylic acid derivatives

Thiazolo[5,4-f]quinoline-8-carboxylic acid derivatives having either the general formula (I): ##STR1## wherein R.sub.1 is a lower alkyl group, a lower alkenyl group or a benzyl group; or the general formula (III-a): ##STR2## WHEREIN R.sub.3 is a lower alkyl group and X is a halogen atom; and methods for the preparation thereof. The compounds of the general formula (I) are useful as antibacterial agents against gram-negative and gram-positive bacteria. The compounds of the general formula (III-a) are useful as antifungal agents against eumycetes and also as an intermediate in a peparation of the compounds of the general formula (I).

Thiazolo(5,4-f)quinoline-8-carboxylic acid derivatives

Bisphenoxy carboxylic acid derivatives useful as an antiarteriosclerosis agent with good absorbability and low toxicity, which are novel compounds represented by the general formula, ##STR1## wherein R.sub.1 and R.sub.2 represent hydrogen atoms or lower alkyl groups and A represents ##STR2## (wherein in case R.sub.3 is a hydrogen atom, R.sub.4 represents an amino-lower-alkyl group, an N-lower-alkylaminoalkyl group, a heterocyclic group, or a heterocyclic group-substituted alkyl group; or R.sub.3 and R.sub.4 may join through an intermediary hetero atom to form a heterocyclic group and if said hetero atom is a nitrogen atom, this nitrogen atom can bear a lower alkyl group as a substituent) or ##STR3## (wherein R.sub.5 represents a hydrogen atom, a hydroxyalkyl group or a derivative thereof, and R.sub.6 represents a hydroxyalkyl group or a heterocyclic group; or R.sub.5 and R.sub.6 may join to form a cyclic group, or may join through another intermediary hetero atom to form a heterocyclic group and if said hetero atom is a nitrogen atom, this nitrogen atom can bear a lower alkyl group as a substituent), are prepared by reacting a bisphenoxy acid represented by the general formula, ##STR4## wherein R.sub.1 and R.sub.2 have the same meanings as defined above, or a reactive derivative thereof with a hetero atom-containing alcohol compound represented by the general formula, ##STR5## wherein R.sub.3 and R.sub.4 have the same meanings as defined above, an amine derivative represented by the general formula, ##STR6## wherein R.sub.5 and R.sub.6 have the same meanings as defined above, or a salt thereof. Alternatively, the bisphenoxy carboxylic acid derivatives represented by the said general formula (I), wherein A is ##STR7## R.sub.5 is hydrogen and R.sub.6 is a hydroxyalkyl group, are prepared by heating a bisphenoxy acid derivative represented by the general formula, ##STR8## wherein R.sub.1 and R.sub.2 have the same meanings as defined above and X represents an alkylene chain.

Novel bisphenoxy carboxylic acid derivatives and their salts

Novel compounds having the formula, ##SPC1## Wherein R.sub.1, R.sub.2 and R.sub.3 are each independently hydrogen or a C.sub.1 -C.sub.4 alkyl; n is an integer of 4-6; and Y is hydrogen or a group of the formula ##EQU1## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above. These compounds are produced, for example, by reacting a bisphenolic compound of the formula, ##SPC2## With chloroform and a ketone compound of the formula,

Cycloalkyl phenoxy carboxylic acid derivatives

Thiazolo[5,4-f]quinoline-8-carboxylic acid derivatives having either the general formula (I): ##SPC1## wherein R.sub.1 is a lower alkyl group, a lower alkenyl group or a benzyl group; or the general formula (III-a): ##SPC2## Wherein R.sub.3 is a lower alkyl group and X is a halogen atom; and methods for the preparation thereof. The compounds of the general formula (I) are useful as antibacterial agents against gram-negative and gram-positive bacteria. The compounds of the general formula (III-a) are useful as antifungal agents against eumycetes and also as an intermediate in a preparation of the compounds of the general formula (I).

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Takarazuka, Japan

Eiichi Murayama